1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Mercapto-3-methyl-6-(pyrimidin-4-YL)-3H-pyrimidin-4-one

HRID 2063341Notes

Reaction equation

HRID 2063341 reaction equation
O=[C:2]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][N:10]=1)[CH2:3][C:4]([O:6]CC)=O.[CH3:15][NH:16][C:17]([NH2:19])=[S:18].N12CCCN=C1CCCCC2>C(O)C>[SH:18][C:17]1[N:16]([CH3:15])[C:4](=[O:6])[CH:3]=[C:2]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][N:10]=2)[N:19]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2723704MethylthioureaHCID 11961458Ethyl 3-oxo-3-(pyrimidin-4-yl)propanoate2×

Product 1

HCID 1784816782-Mercapto-3-methyl-6-(pyrimidin-4-YL)-3H-pyrimidin-4-oneYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 3-oxo-3-(pyrimidin-4-yl)propionate (intermediate 6, 36.10 g, 0.186 mol), N-methylthiourea (25.40 g, 0.282 mol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (29.11 g, 0.191 mol) in ethanol (150 ml) was refluxed for 21 hours. A half amount of ethanol was evaporated under reduced pressure and hydrochloric acid was added. The resulting precipitate was collected by filtration, washed with water and dried. The precipitate was stirred in hot ethyl acetate (1000 ml), and the precipitate was collected by filtration and dried to give 2-mercapto-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (intermediate 7, 33.91 g, 83%).

Workup

  1. customA half amount of ethanol was evaporated under reduced pressure and hydrochloric acid
  2. additionwas added
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customdried
  6. filtrationthe precipitate was collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-eefaaa6bd9b6412e9f14485557b63839
Source dataset
uspto-grants-2012_10
Patent number
US08288383B2

Reaction notes

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